Studies of Peptide Antibiotics. XVI. Analogs of Gramicidin S Containing β-Alanine in Place of L-Proline

スポンサーリンク

概要

• 論文の詳細を見る

• 5,5′-β-alanine-gramicidin S having a larger ring size by two methylene groups than that of gramicidin S was synthesized to investigate the contribution of the ring size of gramicidin S to antibacterial activity. Cyclization of a protected linear decapeptide active ester in pyridine gave the protected 5,5′-β-alanine-gramicidin S in a good yield. The product obtained after the cyclization of a protected linear pentapeptide active ester consisted of the protected 5-β-alanine-cyclosemi and 5,5′-β-alanine-gramicidin S. Pure compounds were obtained by column chromatographic separation of Sephadex LH-20. Hydrogenolysis of these protected cyclic peptides in the presence of hydrogen chloride afforded crystalline hydrochlorides of cyclic deca- and pentapeptide. These hydrochlorides exhibited no antibacterial activity against any of the microorganisms tested. Optical rotatory dispersion measurements of these peptides were also carried out.

• 公益社団法人 日本化学会の論文

著者

• Waki Michinori

  Laboratory Of Biochemistry Department Of Chemistry Faculty Of Science Kyushu University

• Izumiya Nobuo

  Laboratory Of Biochemistry Faculty Of Engineering Kyushu Sangyo University

• Matsuura Shuji

  Laboratory of Biochemistry, Faculty of Science, Kyushu University

• Makisumi Satoru

  Laboratory of Biochemistry, Faculty of Science, Kyushu University

関連論文

• INTERACTION OF HIGHLY BIOACTIVE GRAMICIDIN S ANALOG LACKING HYDROPHILIC AMINO ACID RESIDUES WITH BIOMEMBRANES
• RESOLUTION OF AMINO ACIDS (XVI) : PREPARATION OF FOUR OPTICAL ISOMERS OF δ-HYDROXYLYSINE
• WALDEN INVERSION OF AMINOACIDS (VIII) : STEREOSPECIFIC SYNTHESES OF D-ISOSERINE AND D-ISOTHREONINE FROM L-SERINE AND L-THREONINE
• Inactivation of Gramicidin S by Acylation of Two Ornithine Residues with Higher Fatty Acids
• Development of Electrochemical Protease Assay
• Direct Modification of mRNA by Ferrocenyl Carbodiimide and Its Application to Electrochemical Detection of mRNA
• Interaction Analysis of the Carcinoembryonic Antigen (CEA) with Its Monoclonal Antibody Immobilized on a Gold Surface Using Fourier Transform Infrared Reflection-Absorption Spectroscopy (FT-IR RAS)
• Electrochemical Detection of a Disease-specific Isoform of the Prion Protein (PrP^)
• Analysis of the interaction between trypsin and sunflower trypsin inhibitor (SFTI-1) immobilized on the gold surface
• Immobilization of a peptide probe by a peptide-nucleotide conjugate (PNC)
• Syntheses and Antibacterial Activities of Gramicidin S Analogs Containing L-Ornithine in Place of L-Valine
• Efficient synthesis of a new amino acid, (2S,3R,4R)-4-chloro-3-hydroxyproline.
• Studies of bitter peptides from casein hydrolyzate. X. Synthesis and bitter taste of H-Arg-Gly-Pro-Phe-Pro-Ile-Ile-Val-OH corresponding to C-terminal portion of .BETA.-casein.
• Synthesis of unusual aromatic L-amino acids by asymmetric hydrogenation of cyclic dehydrodipeptides.
• Cyclic peptides. XXIII Synthesis of retro-enantio-AM-toxin I.
• Opioid activities of morphiceptin analogs derived from human .BETA.-casein.
• Synthesis of a Lactam Analog of AM-Toxin I
• Racemization during the synthesis of histidine-containing peptides.
• Studies of Peptide Antibiotics. XVIII. The Synthesis of Tyrocidine E
• Facile synthesis of (2R,3R)-phenylalanine-2,3-d2 and NMR study on deuterated gramicidin S.
• Resolution of amino acids. XII. Preparation of L-2-amino-5-arylpentanoic acids, constituent amino acids in AM-toxins.
• Studies of Peptide Antibiotics. XXIV. Synthesis of 4,4′-D-Alanine-gramicidin S
• Design and synthesis of amphiphilic basic peptides with antibacterial activity and their interaction with model membrane.
• Ribonuclease T1 Peptides. IV. Synthesis of a Protected Heptapeptide Corresponding to Sequence 17–23
• Syntheses of derivatives of N2-acetyl-N3-glycyl-L-2,3-diaminopropionic acid and their hydrolyses by trypsin.
• Synthetic identification of bitter heptapeptide in tryptic hydrolysate of casein.
• Resolution of .ALPHA.-formyl-.EPSILON.-acyl-DL-lysines by acylase.
• Studies of Peptide Antibiotics. XX. Synthesis of Tyrocidine B
• Synthesis of four diastereoisomers of histopine.
• Studies of Peptide Antibiotics. XVI. Analogs of Gramicidin S Containing β-Alanine in Place of L-Proline
• Studies on separation of amino acids and related compounds. VIII. Preparative separation of isomeric L-aspartyl-L-phenylalanine methyl esters and related dipeptide esters by ion-exchange chromatography.
• Studies of peptide antibiotics. XXXVI. Synthesis and biological activity of [5,5'-leucine]-gramicidin S2.
• Studies of peptide antibiotics. XXXVIII. Synthesis of S,S'-bi([1-L-hemicystine]-gramicidin S), a dimerized analog of gramicidin S.
• Different acyl specificity between mold and kidney acylases: Correlation of hydrolytic rate to molecular size and electronegative property of acyl group in acyl-L-phenylalanine hydrolysis.
• Configuration of alanine part in natural octopine.
• Facile synthesis of cyclic dipeptides and detection of racemization.
• Syntheses of cyclic decapeptides with four ornithyl residues related to gramicidin S.
• Studies on Separation of Amino Acids and Related Compounds. VII. Separation of L-Aspartyl-(α,β)-L-histidine and of L-Glutamyl-(α,γ)-L-histidine
• Studies of Peptide Antibiotics. XXXI. Syntheses of iso-Gramicidin S and iso-[2,2′-Lysine]-Gramicidin S
• Studies of peptide antibiotics. XLV. Syntheses of gramicidin S-like analogs with macro-ring structures.
• Studies on Separation of Amino Acids and Related Compounds. V. A Racemization Test in Peptide Synthesis by the Use of an Amino Acid Analyzer
• Studies of peptide antibiotics. XXXVII. Synthesis of [1,1',3,3'-L-alanine]-gramicidin S.
• Studies of Peptide Antibiotics. XXVIII. Syntheses of Sesquigramicidin S and Digramicidin S
• Studies of peptide antibiotics. XXXIX. Syntheses of gramicidin S analogs containing L-histidine in place of L-ornithine.
• Studies of Peptide Antibiotics. XXV. Synthesis of an Immediate Precursor of Gramicidin S
• Studies of Peptide Antibiotics. XIX. Syntheses of 1,1′-Leucine-gramicidin S and 1-Leucine-cyclosemigramicidin S
• Synthesis of N-Terminal Nonapeptide of Trypsinogen and Its Hydrolysis by Trypsin
• Studies of peptide antibiotics. XXXV. Synthesis of gramicidin S by a fragment solid-phase method.
• Studies of Peptide Antibiotics. XXIII. Syntheses of Linear Decapeptide Analogs with Gramicidin S Sequence
• Stereospecific synthesis of D-isothreonine from L-threonine.
• Studies of Peptide Antibiotics. XXX. Syntheses of Gramicidin S Analogs Containing N-Methylleucine in Place of Leucine
• Studies of peptide antibiotics. XXXIII. Syntheses of gramicidin S analogs containing N-methyl-L-valine in place of L-valine.
• Synthesis of .ALPHA. substance-IB in Saccharomyces cerevisiae.
• Synthesis of cyclo-Diglycyl-L-tyrosyl-diglycyl-L-tyrosyl and Hydrolysis by Chymotrypsin
• Cyclic peptides. IV. Synthesis of diastereomeric dihydro-AM-toxin I and its analogs.
• Studies of peptide antibiotics. XXXIV. Syntheses of tyrocidine A and its analogs containing glycine.

もっと見る 閉じる

スポンサーリンク